Synlett 2017; 28(14): 1828-1834
DOI: 10.1055/s-0036-1588982
letter
© Georg Thieme Verlag Stuttgart · New York

FeCl3·6H2O-Catalyzed Tandem Alkylation–Hydrolysis Reaction of Chain α-Oxo Ketene Dithioacetals with Alcohols: Efficient ­Synthesis of α-Alkylated β-Oxo Thioesters

Haifeng Yu*
a   School of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning 11400, P. R. of China   Email: yuhf68105@sina.com
b   Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun, Jilin 130024, P. R. of China
,
Lijuan Zhao
a   School of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning 11400, P. R. of China   Email: yuhf68105@sina.com
,
Quanping Diao
a   School of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning 11400, P. R. of China   Email: yuhf68105@sina.com
,
Tiechun Li
a   School of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning 11400, P. R. of China   Email: yuhf68105@sina.com
,
Peiqiu Liao
b   Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis, Department of Chemistry, Northeast Normal University, Changchun, Jilin 130024, P. R. of China
,
Dongyan Hou
a   School of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning 11400, P. R. of China   Email: yuhf68105@sina.com
,
Guang Xin*
c   College of Food Science, Shenyang Agricultural University, Shenyang 110161, P. R. of China   Email: xguang212@163.com
› Author Affiliations
Supported by: We are grateful to the Fundamental Research Funds for the Jilin Province Key Laboratory of Organic Functional Molecular Design & Synthesis (130028652)
Supported by: the National Nature Science Foundation of China (20902010)
Supported by: Natural Science Foundation of Liaoning Province (201602002)
Supported by: and the Foundation of Liaoning Province Education Administration (L2015003)
Further Information

Publication History

Received: 31 January 2017

Accepted after revision: 05 March 2017

Publication Date:
11 April 2017 (online)


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Abstract

A novel FeCl3·6H2O-catalyzed tandem Friedel–Crafts alkylation–hydrolysis reaction between chain α-oxo ketene dithioacetals and alcohols to afford α-alkylated β-oxo thioesters has been successfully developed. The reaction is efficient in the presence of catalyst loading as low as 30 mol% in MeCN at room temperature, and a wide variety of α-alkylated β-oxo thioesters are efficiently synthesized in good yields.

Supporting Information